Water → 3-(2-chlorophenyl)-7-methylthio-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[C:17]([CH2:18]Br)=[CH:16][N:15]=[C:14]([S:20][CH3:21])[N:13]=1)=[O:10].C[Si](C)(C)N[Si](C)(C)C.O>CN1CCCC1=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:18][C:17]2[C:12](=[N:13][C:14]([S:20][CH3:21])=[N:15][CH:16]=2)[NH:11][C:9]1=[O:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
To a suspension of [(2-chlorophenyl)amino]-N-[5-(bromomethyl)-2-methylthiopyrimidin-4-yl]carboxamide (1360 g, 3.62 mole) of in 10 L 1-methyl-2-pyrrolidinone was added 136 mL hexamethyldisilazane. The mixture was heated to an internal temperature of 105-115° C. for 1.5 hours. The mixture was then cooled to 30° C. and treated with 20L water. The mixture was then stirred at 5-8° C. for 2 hours and filtered. The filters were collected and washed sequentially with water and hexanes. The product was placed in a drying oven and heated under vacuum for 16 hours to give 780 g (70.1%) of 3-(2-chlorophenyl)-7-methylthio-3,4-dihydropyrimido[4,5-d] pyrimidin-2(1H)-one (sulfide 10.1) as an off-white solid. (M+1 308)
Workup
- temperatureThe mixture was then cooled to 30° C.
- filtrationfiltered
- customThe filters were collected
- washwashed sequentially with water and hexanes
- customThe product was placed in a drying oven
- temperatureheated under vacuum for 16 hours
Sources & evidence
- ORD record
- ord-d99bc270273a45a29faf55b47a54dc67
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06451804B1
Reaction notes
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